1081-77-2Relevant articles and documents
Copper-catalyzed cross-coupling reaction of Grignard reagents with primary-alkyl halides: Remarkable effect of 1-phenylpropyne
Terao, Jun,Todo, Hirohisa,Begum, Shameem Ara,Kuniyasu, Hitoshi,Kambe, Nobuaki
, p. 2086 - 2089 (2007)
(Chemical Equation Presented) A general get-together: The Cu-catalyzed cross-coupling reaction of primary-alkyl halides with primary-, secondary-, and tertiary-alkyl and phenyl Grignard reagents proceeds efficiently in THF under reflux in the presence of 1-phenylpropyne (see scheme). The reaction is also applicable to alkyl mesylates (OMs) and tosylates (OTs). The reactivities of alkyl-X with a Grignard reagent increase in the order X = Cl F OMs OTs Br.
New efficient nickel- and palladium-catalyzed cross-coupling reactions mediated by tetrabutylammonium iodide
Piber, Michael,Jensen, Anne Eeg,Rottlaender, Mario,Knochel, Paul
, p. 1323 - 1326 (1999)
(formula presented) The addition of Bu4NI has been found to accelerate the palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates. Remarkably, it further allows a new nickel(0)-catalyzed cross-coupling between functionalized benzylic zinc reagents and primary alkyl iodides leading to polyfunctional products in good yields under mild reaction conditions (0-20 °C, 4-16 h).
NHC-Iridium-Catalyzed Deoxygenative Coupling of Primary Alcohols Producing Alkanes Directly: Synergistic Hydrogenation with Sodium Formate Generated in Situ
Lu, Zeye,Zheng, Qingshu,Yang, Siqi,Qian, Chun,Shen, Yajing,Tu, Tao
, p. 10796 - 10801 (2021/09/08)
The direct conversion of alcohols into long-chain alkanes is an attractive but extremely challenging approach for biomass upgrading. Here, we describe the highly selective deoxygenative coupling of aryl ethanols with primary alcohols to produce alkanes, using a bis-N-heterocyclic carbene iridium (bis-NHC-Ir) complex as the catalyst. Up to quantitative yields and selectivity with a broad substrate scope are attained in both homo- and cross-coupling reactions. Mechanistic studies reveal that the further synergistic hydrogenation of the alkene intermediates by the formate generated in situ in the presence of bis-NHC-Ir is crucial for alkane production.
Nickel-Catalyzed Regioselective Hydroalkylation and Hydroarylation of Alkenyl Boronic Esters
Bera, Srikrishna,Hu, Xile
supporting information, p. 13854 - 13859 (2019/08/26)
Metal hydride catalyzed hydrocarbonation reactions of alkenes are an efficient approach to construct new carbon–carbon bonds from readily available alkenes. However, the regioselectivity of hydrocarbonation remains challenging to be controlled. In nickel hydride (NiH) catalyzed hydrocarbonation, linear selectivity is most often obtained because of the relative stability of the linear Ni–alkyl intermediate over its branched counterpart. Herein, we show that the boronic pinacol ester (Bpin) group directs a Ni-catalyzed hydrocarbonation to occur at its adjacent carbon center, resulting in formal branch selectivity. Both alkyl and aryl halides can be used as electrophiles in this hydrocarbonation, providing access to a wide range of secondary alkyl Bpin derivatives, which are valuable building blocks in synthetic chemistry. The utility of the method is demonstrated by the late-stage functionalization of natural products and drug molecules, the synthesis of an anticancer agent, and iterative syntheses.
